Designer Spotlight is a regular column focusing on style/design and the professional woman.

The new Silicon Valley fashion-tech startup led by Purva Gupta is winning awards right out of the gate, including one from the coveted SXSW Accelerator Pitch Event. It launched its groundbreaking free iOS shopping app, Lily, just weeks ago. Lily is the first fashion shopping search engine to recognize the vital role emotions play in a woman’s buying decisions, particularly how she perceives a specific clothing item will suit her body.

Gupta and fellow Lily founder, CTO Sowmiya Chocka Narayanan, spent two years building the app before going live, which included more than 10,000 hours of research interviews with women to help further develop Lily’s proprietary algorithms.

The company is young yet steadfastly building its database – searching for Pants just became an option last week adding to Dresses and Tops categories.

Before Lily’s SXSW win in Social & Culture category, it raised funds from investors such as Unshackled Ventures, InnoLinks Ventures, retail tech entrepreneur Steve Russell, and former Airbnb Head of Global Operations Varsha Rao, among others. Since, Lily has gone on to win Startup Conference’s Best Startup Award and guest speak at TEDx.

Prior to Lily, Gupta was a Project Manager for Unicef’s Innovation Fund after earning her MBA in Finance from Indian School of Business and her BA in Economics from Shri Ram College of Commerce. Narayanan worked as a Box Senior Software Engineer, a Pocket Gems Mobile Engineer, and a Yahoo! Software Developer after earning her Master’s in Electrical & Computer Engineering from The University of Texas at Austin and her BTech in Information Technology from India’s PSG College of Technology.

Kristina Moore: Why do you think your app won the SXSW Accelerator Pitch Event? What made it stand out and earn Lily the award…which is such a big deal?

Purva Gupta: At Lily, we have built the first ever ‘Perception & Empathy’ engine that decodes a woman’s emotional and perceptive needs to accentuate and de-emphasize certain parts of the body and uses machine learning to match emotions, preferences, and perceptions about her body to clothes from her favorite stores - in real time from both online and offline stores.

There have been many initiatives by brands and celebrities to educate and enlighten women about how they should feel beautiful in their skin, body type, etc., but it hasn’t been actionable on a woman’s next shopping trip. Lily not only recommends clothes that will necessarily flatter their body type, but also helps them feel their best with one clothing recommendation at a time. It’s giving actionable personal styling and instilling confidence with every single interaction using one of the most innovative proprietary technology developed by Lily using emotional intelligence and artificial intelligence.

Lily Cofounder Purva Gupta.Lily

How does Lily’s app work and why might it be attractive to the busy professional?

Gupta: The experience is as simple as texting with a friend about clothes, but the deep technology and expertise the app leverages leads to helping women look and feel their best, everyday!

To begin with, the app asks users a few quick questions about body type, style preferences and how they perceive their body - one example of a question Lily asks: “How would you describe your décolleté (that’s French for chest — I’m very worldly!)?” Then it recommends clothes, as per what the user is looking for, from her favorite stores that will flatter her body and perceptions. With every like/dislike of the user, Lily learns and makes the next set of recommendations better. The level of detail that Lily understands is almost impossible for a human stylist to understand from hundreds and thousands of products people browse on Lily. Lily is able to do this, because our technology enables us to understand deep attributes about every single item of clothing available on Lily.

Yet, Lily prides herself in making the woman understand how every single item of clothing recommended to her by Lily flatters her individual body type and minute details she shared with Lily, just like how a great human stylist would do. Yes, every single item, in real-time.

The users can then buy from within the app and experience an easy universal checkout. Lily also keeps a track of shipping, returns, refunds and everything else in between. For busy professionals, the idea of finding the clothes along with the simplest buying experience is a huge time saver, plus something that can easily become a habit.

Gupta: In the earliest days of my journey in 2015, I questioned myself almost everyday, “Why does the world need another fashion app?” To get to the answer quickly, I personally spent more than 10,000 hours in the last two years asking women about what they feel when they are buying clothes online or in-stores and why they buy the clothes they buy. I found a behavioral secret. It was super simple.“95% women were looking for clothes that would accentuate certain parts of their body and de-emphasize certain other parts.”

Actually, the origin of this secret was in human behavior. I learned that girls start recognizing themselves in the mirror at the age of two and since that time, they start disliking parts of their body. In their teen years, they start making perceptions about their body (thighs, tummy etc.) relative to the physical appearance of their moms, friends and celebrities. These perceptions form insecurities. On an average, women in the U.S. have 13 negative thoughts about their body every day! While shopping, women look for certain types of clothes, sometimes even subconsciously, that address their insecurities.

We quickly understood that most clothing recommendation engines are focusing on 'what' users like and buy through millions of tangible actions, rational data points, such as browse history, purchase history, etc. What we learned from thousands of conversations was personalization engines focus on 'why' users like what they like yet don’t understand their intangible perceptions, irrational behavior, which drive their purchase decisions. This is how we built the core emotional intelligence technology at Lily.

How does Lily break through a woman’s style bias on fashions that actually look favorable on her?

Gupta: At Lily, the definition of emotion we use is the perception gap between reality and expectation. When the gap is positive, there is confidence and when the gap is negative, there is insecurity. In the first few minutes of a user’s interaction with Lily, we try to understand where the perception gaps lie for every part of the user’s body. Lily asks how the user feels about her body - what parts she likes to accentuate and which ones she’d prefer to minimize - and then uses a complex matching algorithm to make recommendations. To close the loop and gain the user’s trust, Lily always explains how every item of clothing flatters the user’s body and perceptions.

The power of this idea lies in the mix of science and organically ingraining positivity in their mindset everyday. The focus is on their best assets instead of focusing on what they think are their worst. To the effect that our users have reported that it’s almost become a habit for them to read why an item of clothing flatters them, which actually makes them feel great about buying and wearing those items. Some of our users say- “it’s boring to shop on a ‘regular’ website now, as I’m constantly looking for where my personalized recommendation of how this best flatter me is.”

Lily’s personalized search results include fashion tips.

How has style influenced your self-confidence? How a game changer?

Gupta: In the 4th grade, I developed an inferiority complex that turned into an acute stammer when I moved from a small town in India to a big city full of sophisticated people. People who I thought were much more sophisticated than me.

Just because I could not speak in fluent English like my other friends, I developed an inferiority complex. I struggled for eight years to overcome this mental barrier and insecurity that manifested in one singular thought: I am not good enough. I excelled at everything academically because books are all I could turn to. So I decided to overcome my fear by facing it everyday. I forced myself to address large groups of people wherever possible. I was fortunate that my school and teachers helped me tremendously. I would video tape myself to see where I needed improvements and keep pushing myself, striving to be what I deemed was ‘better.’

In the end, what helped me the most was conditioning my mind to feel more beautiful, and hence, more confident. And through that process, I repeatedly did one thing - dressing to feel my best. Somehow, the power of looking and feeling my best, changed everything.

Overcoming my own powerful insecurity is one of my biggest achievements in life - and the feeling of empowerment it gave me lead me to an insight I hope will help other young women.

It’s my understanding Lily’s user buying conversion rate is 27%; where the usual is 1%. Why do you think that is?

Gupta: Because we are understanding a woman's emotions about her body and her clothes. We found in our research that women are buying more clothes every now and then to feel their best in the situation they are in or preparing for! Whether it’s that meeting with the SVP, a special dinner party, a job interview or just for everyday occasions – it’s all about satisfying those feelings. And we feel through Lily, we can help women look and feel the best version of themselves. In the last 13 weeks since we have been available in the app store, 1 in 3 users have already bought from their favorite retailers, such as Nordstrom, Banana Republic, Ann Taylor, ASOS, Revolve, Macy’s, H&M, Forever 21, Bloomingdales, Mango, Lulus, Eloquii, Modcloth, Express, Loft among others.

A sample search via Lily’s unique shopping app.Lily

What inspired you to collaborate with Sowmiya Chocka Narayanan to found Lily?

Gupta: I met Sowmiya at the incubator, Founder Institute. She had also reached out to me on LinkedIn regarding guidance on another idea she was working on then - but 90% of our follow up conversation ended up being about Lily and the rest is history. I knew I found the perfect partner when we immediately aligned on the vision and the problem was already keeping her awake in the night.

Sowmiya is a super strong founder, very comfortable and confident in the path she sets foot on. I realized her strength and determination on day one when I discovered Sowmiya had already left her job at Box before she even knew exactly what our startup would be about in spite of the fact that she had a 13 month old son at home. With strong fundamentals, her quality to simplify complex problems has led us to successfully build some of the deepest tech using emotional intelligence and artificial intelligence. Always being on the edge yet marching away with the most calm look on her face, is another place I get my daily doze of inspiration from her.

Lily’s team consists of all-women. Was this intentional? If so, why?

Gupta: Lily is built by women to empower women to be the best version of themselves. As we have come to realize that more than 150 million women in this country are not happy with their appearance and women get 13 negative thoughts about their body everyday, as a team, we are on a mission to change these numbers and solve this problem in the world. Today, our mission is to turn each of the 13 negative thoughts she sees in her reflection every day, positive.

That said, No, it wasn’t intentional. Just that it was more logical for women to relate to the problem and be a part of a movement that will change this forever for women. We are on our way to hire our first male engineers and data scientists and happily so!

Why the name, Lily?

Gupta: We were looking for the simplest universal, short name, with a sound and feminine association to it and one that symbolizes inner beauty and purity. There you go - Lily!

Any plans to make Lily app Android friendly?

Gupta: Absolutely! Coming up soon.

What is your current biggest challenge as a fashion-tech startup?

Gupta: We currently have only three categories of clothing on Lily – Tops, Dresses, and Pants. As more users love the Lily experience, we are getting requests for new categories like shorts, jackets, activewear, etc. and more brands/retailers to be on Lily asap. While we are hard at work launching those categories and brands/retailers, we know it’s a good challenge to have!

What’s next? Where do you see Lily in three years?

Gupta: Adding more categories, stores and features that will help women to embrace their beautiful, unique body and let clothes positively define their self-confidence.

We are positioning ourselves to be the experience layer of fashion retail - the one stop destination that gets you and your clothing needs from your favorite retailers. In the next 3 years, we aim to become that for millions of women in this country.

How do you replenish your creativity and energy?

Gupta: You will be surprised, I energize myself in the day by reading all the feedback and especially the love letters from our users! At Lily, we are all about the empathy and we love to hear how it’s making a difference!

Other than that, I really enjoy taking long walks and getting distracted by nature. It’s very hard to do that all hours of the day, but an hour or two early in the morning or late in the evening is where I try to condition my mind to just be in the moment and not think about work. Again, on most days! I have also recently jumped on the yoga and meditation train - I’m starting to think the hype may be all true. Lastly, since my better half is also an economist, we love to think about the big picture about any industry - in some ways, that ideation exercise is always inspiring, energizing and pushing us to the next level.

Kristina Moore is a style expert focusing on visual presentation as a dynamic professional tool. She is the founder and editor of Corporate Fashionista.

I’m the founder and editor of Corporate Fashionista, a fashion blog for professional women focusing on how to use what you wear as an effective business tool. I began my career in accounting and finance working in a variety of industries from the casual high tech arena to th...